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Lake Ontario to Florida, Keys & caribbean
I just finished a very similar trip from Chicago, through the lakes to Tonowanda, where we entered the erie canal. After seven months, we arrived in sw florida. It is a great trip. I, however, caution you that it is a long way, so don''t dilly-dally too much.
The biggest challenge will probably be the NJ stretch from Sandy Hook to Cape May, then the run up the Delaware Bay, as you sort of have to commit to the distance once you start.
The Chesapeake is worth spending time in. I wish I''d have gottent there sooner so I could have spent more time in better weather. October was already plenty cold, which bring up another question: What are you going to do for heat? We have a diesel cabin heater that helped us to greatly extend our cruising time in colder climates when every one else had already been forced south.
The ICW is porous enough to decided to jump out and make big runs off shore, or day sails out side, or motorsailing inside. It allowed us to move every day we wanted to.
I kept a web site of out trip, which may or may not be useful to you: www.nereus32.com. However, you can contact me through the site and I''d be happy to answer any question pertaining to what I did and the reasons I did them.
Good luck with the trip. It is the best thing I ever did!